Ethyl Acetate → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

HRID 851584ノート

反応式

HRID 851584 の反応式
P(Cl)(Cl)Cl.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:8]2[S:7]1=O.C(OCC)(=O)C>CN(C)C=O>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][C:16]([Cl:17])([Cl:18])[Cl:19])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@H:8]2[S:7]1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 705266812,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide

生成物 1

HCID 705273932,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate収率 61.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Phosphorus trichloride (0.5 ml.) was dropwise added under ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide (0.72 g.) in dimethylformamide (5 ml.) and the mixture was stirred for 1 hour at the same temperature. After the reaction, the reaction mixture was poured into a mixture of ethyl acetate (40 ml.) and ice-water (40 ml.), and the ethyl acetate layer was separated. The aqueous layer was further extracted with ethyl acetate (10 ml.), and the ethyl acetate layer was combined. The combined solution was washed in turn with 5% hydrochloric acid, a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The dried solution was treated with activated charcoal and the solvent was distilled off. The residue was crystallized with a small amount of ether to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (0.43 g.), mp 175° to 178° C.

後処理

  1. customAfter the reaction
  2. customthe ethyl acetate layer was separated
  3. extractionThe aqueous layer was further extracted with ethyl acetate (10 ml.)
  4. washThe combined solution was washed in turn with 5% hydrochloric acid
  5. dry with materiala sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  6. additionThe dried solution was treated with activated charcoal
  7. distillationthe solvent was distilled off
  8. customThe residue was crystallized with a small amount of ether

出典と根拠

ORDレコード
ord-93cc260fcfa440f88e4c71f894c6108b
出典データセット
uspto-grants-1983_05
特許番号
US04385176

反応ノート

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